2-Chloro-6-methylpyrazine → HCID 71536681, 화합물

HRID 1503269노트

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HRID 1503269 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18]#[CH:19])([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].Cl[C:24]1[CH:29]=[N:28][CH:27]=[C:26]([CH3:30])[N:25]=1>C(N(CC)CC)C.C(#N)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18]#[C:19][C:24]4[CH:29]=[N:28][CH:27]=[C:26]([CH3:30])[N:25]=4)([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6]

참가 물질

8

반응물 2

HCID 71700952-Chloro-6-methylpyrazineHCID 117702457HCID 117702457, 화합물

생성물 1

HCID 71536681HCID 71536681, 화합물수율 38.9%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

To a stirred mixture of intermediate 8, 3-chloro-N-(3-ethynyl-adamantan-1-yl)-benzamide (60 mg, 0.19 mmol) and 2-chloro-6-methylpyrazine (60 mg, 0.47 mmol) in triethylamine (0.5 mL) and acetonitrile (2 mL) was added Pd(PPh3)4 (3 mg, 0.02 mmol), followed by an addition of CuI (3 mg, 0.016 mmol). After heated at 70° C. for three hours, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (50 mL) and brine, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by Prep HPLC to give 30 mg (38%) of the title compound, 3-chloro-N-[3-(6-methyl-pyrazin-2-ylethynyl)-adamantan-1-yl]-benzamide. 1H NMR (500 MHz, CDCl3): δ 8.57 (brs, 1H), 7.69 (t, J=2.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.35 (t, J=8.0 Hz, 1H), 5.78 (s, 1H), 2.57 (s, 3H), 2.40 (s, 2H), 2.25 (s, 2H), 2.17-2.15 (m, 2H), 2.06-1.96 (m, 6H), 1.73-1.70 (m, 2H); ESI-MS m/z: 406 (M+H)+.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with water (50 mL) and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by Prep HPLC

출처 및 근거

ORD 기록
ord-254246cb506448babd87e54e5031f5b5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212165B2

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